Editing Anethole (section)

== Research ==
=== Antimicrobial and antifungal activity ===
Anethole has potent [[antimicrobial]] properties, against [[bacteria]], [[yeast]]s, and [[fungi]].<ref name="pmid11807977">{{cite journal|last1=De|first1=M.|last2=De|first2=A. K.|last3=Sen|first3=P.|last4=Banerjee|first4=A. B.|title=Antimicrobial properties of star anise (''Illicium verum'' Hook. f.)|journal=Phytotherapy Research|volume=16|issue=1|pages=94–95|date=2002|pmid=11807977|doi=10.1002/ptr.989|s2cid=27196549}}</ref> Reported antibacterial properties include both [[bacteriostatic]] and [[bactericidal]] action against ''[[Salmonella enterica]]''<ref name="pmid11743758">{{cite journal|last1=Kubo|first1=I.|last2=Fujita|first2=K.|title=Naturally occurring anti-''Salmonella'' agents|journal=Journal of Agricultural and Food Chemistry|volume=49|issue=12|pages=5750–5754|date=2001|pmid=11743758|doi=10.1021/jf010728e|bibcode=2001JAFC...49.5750K }}</ref> but not when used against ''Salmonella'' via a [[fumigation]] method.<ref name="pmid11307877">{{cite journal|last1=Weissinger|first1=W. R.|last2=McWatters|first2=K. H.|last3=Beuchat|first3=L. R.|title    = Evaluation of volatile chemical treatments for lethality to ''Salmonella'' on alfalfa seeds and sprouts|journal=Journal of Food Protection|volume=64|issue=4|pages=442–450|date=April 2001|pmid=11307877|doi=10.4315/0362-028X-64.4.442|doi-access=free}}</ref> Antifungal activity includes increasing the effectiveness of some other [[phytochemical]]s (such as [[polygodial]]) against ''[[Saccharomyces cerevisiae]]'' and ''[[Candida albicans]]'';<ref name="pmid17078111">{{cite journal|last1=Fujita|first1=K.|last2=Fujita|first2=T.|last3=Kubo|first3=I.|title=Anethole, a potential antimicrobial synergist, converts a fungistatic dodecanol to a fungicidal agent|journal=Phytotherapy Research|volume=21|issue=1|pages=47–51|date=2007|pmid=17078111|doi=10.1002/ptr.2016|s2cid=9666596|doi-access=free}}</ref>

''[[In vitro]]'', anethole has [[antihelmintic]] action on eggs and larvae of the [[domestic sheep|sheep]] gastrointestinal [[nematode]] ''[[Haemonchus contortus]]''.<ref name="pmid17629623">{{cite journal|last1=Camurça-Vasconcelos|first1=A. L.|last2=Bevilaqua|first2=C. M.|last3=Morais|first3=S. M.|last4=Maciel|first4=M. V.|last5=Costa|first5=C. T.|last6=Macedo|first6=I. T.|last7=Oliveira|first7=L. M.|last8=Braga|first8=R. R.|last9=Silva|first9=R. A.|last10=Vieira|first10=L. S.|title=Anthelmintic activity of ''Croton zehntneri'' and ''Lippia sidoides'' essential oils|journal=Veterinary Parasitology|volume=148|issue=3–4|pages=288–294|year=2007|pmid=17629623|doi=10.1016/j.vetpar.2007.06.012}}</ref> Anethole also has nematicidal activity against the plant nematode ''[[Meloidogyne javanica]]'' in vitro and in pots of [[cucumber seedlings]].<ref name="pmid18944489">{{cite journal|last1=Oka|first1=Y.|last2=Nacar|first2=S.|last3=Putievsky|first3=E.|last4=Ravid|first4=U.|last5=Yaniv|first5=Z.|last6=Spiegel|first6=Y.|title=Nematicidal activity of essential oils and their components against the root-knot nematode|journal=Phytopathology|volume=90|issue=7|pages=710–715|date=2000|pmid=18944489|doi=10.1094/PHYTO.2000.90.7.710|doi-access=free|bibcode=2000PhPat..90..710O }}</ref>

=== Insecticidal activity ===
Anethole also is a promising insecticide. Several essential oils consisting mostly of anethole have [[insecticide|insecticidal]] action against [[larva]]e of the [[mosquito]] ''[[Ochlerotatus]] caspius''<ref name="pmid17368893">{{cite journal|last1=Knio|first1=K. M.|last2=Usta|first2=J.|last3=Dagher|first3=S.|last4=Zournajian|first4=H.|last5=Kreydiyyeh|first5=S.|title=Larvicidal activity of essential oils extracted from commonly used herbs in Lebanon against the seaside mosquito, ''Ochlerotatus caspius''|journal=Bioresource Technology|volume=99|issue=4|pages=763–768|year=2008|pmid=17368893|doi=10.1016/j.biortech.2007.01.026|bibcode=2008BiTec..99..763K }}</ref> and ''[[Aedes aegypti]]''.<ref name="pmid15237942">{{cite journal|last1=Cheng|first1=S. S.|last2=Liu|first2=J. Y.|last3=Tsai|first3=K. H.|last4=Chen|first4=W. J.|last5=Chang|first5=S. T.|title=Chemical composition and mosquito larvicidal activity of essential oils from leaves of different ''Cinnamomum osmophloeum'' provenances|journal=Journal of Agricultural and Food Chemistry|volume=52|issue=14|pages=4395–4400|date=2004|pmid=15237942|doi=10.1021/jf0497152|bibcode=2004JAFC...52.4395C }}</ref><ref name="pmid16646345">{{cite journal|last1=Morais|first1=S. M.|last2=Cavalcanti|first2=E. S.|last3=Bertini|first3=L. M.|last4=Oliveira|first4=C. L.|last5=Rodrigues|first5=J. R.|last6=Cardoso|first6=J. H.|title=Larvicidal activity of essential oils from Brazilian ''Croton'' species against ''Aedes aegypti'' L.|journal=Journal of the American Mosquito Control Association|volume=22|issue=1|pages=161–164|year=2006|pmid=16646345|doi=10.2987/8756-971X(2006)22[161:LAOEOF]2.0.CO;2|s2cid=33429927 }}</ref> In a similar manner, anethole itself is effective against the [[fungus gnat]] ''Lycoriella ingenua'' ([[Sciaridae]])<ref name="pmid16786497">{{cite journal|last1=Park|first1=I. K.|last2=Choi|first2=K. S.|last3=Kim|first3=D. H.|last4=Choi|first4=I. H.|last5=Kim|first5=L. S.|last6=Bak|first6=W. C.|last7=Choi|first7=J. W.|last8=Shin|first8=S. C.|title=Fumigant activity of plant essential oils and components from horseradish (''Armoracia rusticana''), anise (''Pimpinella anisum'') and garlic (''Allium sativum'') oils against ''Lycoriella ingenua'' (Diptera: Sciaridae)|journal=Pest Management Science|volume=62|issue=8|pages=723–728|date=2006|pmid=16786497|doi=10.1002/ps.1228}}</ref> and the [[mold mite]] ''Tyrophagus putrescentiae''.<ref name="pmid15954709">{{cite journal|last1=Lee|first1=H. S.|title=Food protective effect of acaricidal components isolated from anise seeds against the stored food mite, ''Tyrophagus putrescentiae'' (Schrank)|journal=Journal of Food Protection|volume=68|issue=6|pages=1208–1210|date=2005|pmid=15954709|doi=10.4315/0362-028X-68.6.1208|doi-access=free}}</ref> Against the mite, anethole is a slightly more effective [[pesticide]] than [[DEET]], but [[anisaldehyde]], a related natural compound that occurs with anethole in many essential oils, is 14 times more effective.<ref name="pmid15954709" /> The insecticidal action of anethole is greater as a [[fumigation|fumigant]] than as a contact agent. ''trans''-Anethole is highly effective as a fumigant against the [[cockroach]] ''[[Blattella germanica]]''<ref name="pmid11852640">{{cite journal|last1=Chang|first1=K. S.|last2=Ahn|first2=Y. J.|title=Fumigant activity of (''E'')-anethole identified in ''Illicium verum'' fruit against ''Blattella germanica''|journal=Pest Management Science|volume=58|issue=2|pages=161–166|date=2002|pmid=11852640|doi=10.1002/ps.435}}</ref> and against adults of the [[weevil]]s ''[[Sitophilus oryzae]]'', ''[[Callosobruchus chinensis]]'' and [[beetle]] ''[[Lasioderma serricorne]]''.<ref name="pmid11455661">{{cite journal|last1=Kim|first1=D. H.|last2=Ahn|first2=Y. J.|title=Contact and fumigant activities of constituents of ''Foeniculum vulgare'' fruit against three coleopteran stored-product insects|journal=Pest Management Science|volume=57|issue=3|pages=301–306|date=2001|pmid=11455661|doi=10.1002/ps.274}}</ref>

As well as an insect pesticide, anethole is an effective [[insect repellent]] against mosquitos.<ref name="pmid12963152">{{cite journal|last1=Padilha de Paula|first1=J.|last2=Gomes-Carneiro|first2=M. R.|last3=Paumgartten|first3=F. J.|title=Chemical composition, toxicity and mosquito repellency of ''Ocimum selloi'' oil|journal=Journal of Ethnopharmacology|volume=88|issue=2–3|pages=253–260|year=2003|pmid=12963152|doi=10.1016/s0378-8741(03)00233-2}}</ref>

=== Ouzo effect ===
[[File:Preparing absinthe.jpg|thumb|Diluting [[absinthe]] with water produces a spontaneous microemulsion ([[ouzo effect]])]]
Anethole is responsible for the "[[ouzo effect]]" (also "louche effect"), the spontaneous formation of a [[microemulsion]]<ref name="Sitnikova+2005">{{cite journal|last1=Sitnikova|first1=Natalia L.|first2=Rudolf|last2=Sprik|first3=Gerard|last3=Wegdam|first4=Erika|last4=Eiser|year=2005|title=Spontaneously formed ''trans''-anethol/water/alcohol emulsions: Mechanism of formation and stability|journal=Langmuir|volume=21|issue=16|pages=7083–7089|doi=10.1021/la046816l|url=http://www.science.uva.nl/~sprik/personal/pdf/05/la046816l.pdf|access-date=2009-03-15|pmid=16042427|archive-url=https://web.archive.org/web/20090318153610/http://www.science.uva.nl/~sprik/personal/pdf/05/la046816l.pdf|archive-date=2009-03-18|url-status=dead}}</ref><ref>{{cite journal|title=The "Ouzo effect": Following the spontaneous emulsification of ''trans''-anethole in water by NMR|journal=Comptes Rendus Chimie|volume=11|issue=4–5|date=2008|pages=493–498|first1=David|last1=Carteau|first2=Dario|last2=Bassani|first3=Isabelle|last3=Pianet|doi=10.1016/j.crci.2007.11.003|url=https://comptes-rendus.academie-sciences.fr/chimie/articles/10.1016/j.crci.2007.11.003/ }}</ref> that gives many alcoholic beverages containing anethole and water their cloudy appearance.<ref name="Sanchez-Dominguez Rodriguez-Abreu 2016 p. 369">{{cite book|last1=Sánchez Domínguez|first1=M.|last2=Rodríguez Abreu|first2=C.|title=Nanocolloids: A Meeting Point for Scientists and Technologists|publisher=Elsevier Science|year=2016|isbn=978-0-12-801758-6|url=https://books.google.com/books?id=ReXIBAAAQBAJ&pg=PA369|access-date=2018-08-02|page=369|quote= O/W and W/O nano-emulsions can also be formed without a surfactant by self-emulsification, using the so-called Ouzo effect. The major components of Ouzo (a Greek drink) are ''trans''-anethole, ethanol, and water. Anethole is almost insoluble ...}}</ref> Such a spontaneous microemulsion has many potential commercial applications in the food and pharmaceutical industries.<ref name="pmid17229398">{{cite journal|last1=Spernath|first1=A.|last2=Aserin|first2=A.|title=Microemulsions as carriers for drugs and nutraceuticals|journal=Advances in Colloid and Interface Science|volume=128–130|pages=47–64|year=2006|pmid=17229398|doi=10.1016/j.cis.2006.11.016}}</ref>

=== Precursor to illicit drugs ===
Anethole is an inexpensive chemical precursor for [[paramethoxyamphetamine]] (PMA),<ref name="pmid12742705">{{cite journal|last1=Waumans|first1=D.|last2=Bruneel|first2=N.|last3=Tytgat|first3=J.|title=Anise oil as ''para''-methoxyamphetamine (PMA) precursor|journal=Forensic Science International|volume=133|issue=1–2|pages=159–170|year=2003|pmid=12742705|doi=10.1016/S0379-0738(03)00063-X}}</ref> and is used in its clandestine manufacture.<ref name="pmid15240033">{{cite journal|last1=Waumans|first1=D.|last2=Hermans|first2=B.|last3=Bruneel|first3=N.|last4=Tytgat|first4=J.|title=A neolignan-type impurity arising from the peracid oxidation reaction of anethole in the surreptitious synthesis of 4-methoxyamphetamine (PMA)|journal=Forensic Science International|volume=143|issue=2–3|pages=133–139|year=2004|pmid=15240033|doi=10.1016/j.forsciint.2004.02.033}}</ref> Anethole is present in the essential oil from [[guarana]], which has psychoactive effects typically attributed to its caffeine content. The absence of PMA or any other known psychoactive derivative of anethole in human urine after ingestion of guarana leads to the conclusion that any psychoactive effect of guarana is not due to aminated anethole metabolites.<ref name="pmid8765992">{{cite journal|last1=Benoni|first1=H.|last2=Dallakian|first2=P.|last3=Taraz|first3=K.|title=Studies on the essential oil from guarana|journal=Zeitschrift für Lebensmittel-Untersuchung und -Forschung|volume=203|issue=1|pages=95–98|year=1996|pmid=8765992|doi=10.1007/BF01267777|s2cid=45636969}}</ref>

Anethole is also present in [[absinthe]], a [[liquor]] with a reputation for [[Psychedelics, dissociatives and deliriants|psychoactive]] effects; these effects, however, are attributed to [[ethanol]].<ref name="pmid18429531">{{cite journal|last=Lachenmeier|first=D. W.|title=Thujon-Wirkungen von Absinth sind nur eine Legende—Toxikologie entlarvt Alkohol als eigentliche Absinthismus-Ursache|trans-title=Thujone-attributable effects of absinthe are only an urban legend—toxicology uncovers alcohol as real cause of absinthism|language=de|journal=Medizinische Monatsschrift für Pharmazeuten|volume=31|issue=3|pages=101–106|date=2008|pmid=18429531}}</ref> (See also [[thujone]], [[anethole dithione]] (ADT), and [[anethole trithione]] (ATT).)

=== Estrogen and prolactin ===
Anethole has [[estrogen]]ic activity.<ref name="Jordan1986">{{cite book|first=Virgil Craig|last=Jordan|title=Estrogen/Antiestrogen Action and Breast Cancer Therapy|url=https://books.google.com/books?id=7WmLZfGXST0C&pg=PA21|year=1986|publisher=University of Wisconsin Press|isbn=978-0-299-10480-1|pages=21–22}}</ref><ref>{{cite journal |last1=Howes |first1=M.-J. R. |last2=Houghton |first2=P. J. |last3=Barlow |first3=D. J. |last4=Pocock |first4=V. J. |last5=Milligan |first5=S. R. |date=November 2002 |title=Assessment of estrogenic activity in some common essential oil constituents |journal=The Journal of Pharmacy and Pharmacology |volume=54 |issue=11 |pages=1521–1528 |doi=10.1211/002235702216 |issn=0022-3573 |pmid=12495555|s2cid=28650422 |doi-access=free }}</ref><ref>{{cite journal |last=Albert-Puleo |first=M. |date=December 1980 |title=Fennel and anise as estrogenic agents |url=https://pubmed.ncbi.nlm.nih.gov/6999244/ |journal=Journal of Ethnopharmacology |volume=2 |issue=4 |pages=337–344 |doi=10.1016/s0378-8741(80)81015-4 |issn=0378-8741 |pmid=6999244}}</ref> It has been found to significantly increase [[uterine]] weight in immature female rats.<ref name="TisserandYoung2013">{{cite book|first1=Robert|last1=Tisserand|first2=Rodney|last2=Young|title=Essential Oil Safety: A Guide for Health Care Professionals|url=https://books.google.com/books?id=DbEKAQAAQBAJ&pg=PA150|date=2013|publisher=Elsevier Health Sciences|isbn=978-0-7020-5434-1|page=150}}</ref>

Fennel, which contains anethole, has been found to have a [[galactagogue]] effect in animals. Anethole bears a structural resemblance to [[catecholamine]]s like [[dopamine]] and may displace dopamine from its receptors and thereby disinhibit [[prolactin]] secretion, which in turn may be responsible for the galactagogue effects.<ref name="BoneMills2013">{{cite book|first1=Kerry|last1=Bone|first2=Simon Y.|last2=Mills|title=Principles and Practice of Phytotherapy|series=Modern Herbal Medicine|volume=2|url=https://books.google.com/books?id=5V1QlqHazcwC&pg=PA559|year=2013|publisher=Elsevier Health Sciences|isbn=978-0-443-06992-5|page=559}}</ref>